My sister is trying ruin my perfect wedding day. I think she’s going to regret it.

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Dear Prudence,

My fiancé and I are getting married in February on Valentine’s Day. The trouble is that my sister, “Sydney,” has lost her damn mind.

She is demanding that we change the date of our wedding because Valentine’s Day is the day her ex-husband ran off with her best friend. Five years ago. I told her this is insanity and that she needs to move on with her life. Now Sydney is furious with me and accusing me of having no regard for her feelings. I could not change the date of my wedding even if I wanted to. The invitations have been sent, the venue is booked, and everything has been ordered. She is now threatening to boycott the entire event. Should I try to talk some sense into her, or take this as a win?

—She’s Stuck in the Past

Dear She’s Stuck,

If you’d asked me what to do before you got frustrated with your sister and expressed it, I would have encouraged you to be a bit gentler with her. The commentary about insanity and moving on was unnecessary. She’s obviously very hurt (making irrational demands, yes; but in pain, too) and didn’t need to be told anything that would make her feel worse about herself. Also, by criticizing her in that way, you made this into a fight between two sisters rather than one sister acting out. But what’s done is done and honestly, she’d probably be threatening a boycott even if you’d said “I know how much the end of your marriage hurt you, you didn’t deserve it, and I wish I would have known how you felt about Valentine’s Day before we booked everything. At this point, I can’t change the date, but if there is anything I can do to make this day easier for you, please let me know.”

So let her go ahead with her plan to skip the event, but because it sounds like a plan made in a heightened emotional state, make the seating chart flexible enough to give her some room to change her mind—and if she does RSVP yes, don’t say “What happened to the irrational boycott?” Just ask what she wants for her meal.

Dear Prudence,

I have a younger (31) male friend who has been single for many years. He’s a great guy, albeit with some long-standing health issues caused by growing up in an abusive household. I promised that I would help him find a partner, but I don’t know what to do next.

I have no friends to introduce him to—he’s very firmly monogamous, and my female friends are all too old and/or too polyamorous and/or too asexual. He’s adamant that he doesn’t want to use dating apps because our feckless government has recently passed an Online “Safety” Act, which requires adults to submit their IDs to third-party checking sites in order to use “adult” websites. Since this came into law in July, there has already been at least one database breach of 70,000 users including their legal IDs, which is shocking. As a person highly concerned about privacy, he doesn’t want to take this risk and I don’t feel comfortable pressuring him to do so.

The problem is, where do we go next? I’m very willing to go along to an in-person event and be his “wing woman” as it were, offering him moral support as he talks to women in the hope of making friendships which could go further, but what event should this be? Things like speed dating are absolutely terrible for a person who cannot work due to disability, because many people who go to a dating event seem to be hoping for a partner who has a high income and a luxury car.

Suggestions for “where to meet someone” in advice columns always involve finding an activity which you enjoy doing and hoping to make friends there. Well, my friend likes roleplaying games and mountain biking, both of which are extremely male-dominated, and one of which is generally a solo hobby. He doesn’t know what else he “might” be interested in because he doesn’t have a lot of life experience due to his abusive background.

I’ve suggested things like classes of some sort, but he’s either rejected the idea as unhelpful (e.g. dance classes—he doesn’t think anyone his age would be at them), or he’s concerned that other attendees are there to learn, not to look for romance. He doesn’t want to be a creep, so he feels unwilling to sign up for an activity unless there is a reasonable chance of there being women his age who are looking for a boyfriend. He’s not in the least bit religious, and finds the idea of “atheist alternative to church” to be weird.

And I’m just desperate to help but utterly clueless—I have never had to look for a partner in my life due to being a bi poly woman. I’ve just had to exist in nerd space, and I find people. Outside of classes or religious groups, what kind of activities exist where you meet the same people every week/fortnight/month and can get to know them over time? And where it wouldn’t be weird or creepy to attend with your primary purpose being to find a partner?

—Wingman Who Doesn’t Know How to Fly

Dear Wingman,

It’s really fun to think about this and a bunch of ideas come to mind: Sign up for a sip and paint! Hang out at a winery! Wander the farmer’s market and chat people up together! Go to the dog park! But I know your friend is going to reject each of these suggestions. He has—maybe unconsciously—placed so many restrictions on his search for romance that he’s made it practically impossible for you to help him. He won’t use apps. He won’t go to dance classes because of his assumptions about the age of the other people who will be there. He won’t, I assume, attend to speed dating without you escorting him. He won’t participate in anything if there’s not a reasonable chance of finding a girlfriend, if it’s anything like church, if he won’t meet the same people regularly, or if anyone might find it creepy to be there looking for a partner. He won’t even give any information on the qualities he might like in a date.

It’s clear to me that your friend doesn’t really want to put himself out there, either because he doesn’t want a relationship as much as you think he does, or because he’s absolutely terrified of failure or rejection. It sounds like he’s been through a lot and suffered a lot, and may still be really suffering now, so I can understand why his outlook isn’t the most optimistic or open. But that’s going to have to change before he can benefit from the assistance of a wing woman. The best you can do as a friend is to help him find some joy in life and some confidence in himself. Maybe encourage him to join you in having new experiences that could inspire him to feel more excited and less pessimistic and fearful about the possibilities for love. This might fortify him to take some of the risks that come with dating. Plus, knowing himself better, being happier, and liking his life will make him more attractive when he does decide to put himself out there and look for a partner.

I want to be careful of suggesting that he needs to be fully healed and self-actualized in order to find a partner, because he doesn’t. But he has to be healed and self-actualized enough to be willing to try. And he’s not there yet. The search won’ t work if you want this for him more than he wants it for himself.

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Dear Prudence,

I have a great connection with a colleague; we’re both single, and we’ve fooled around a little too. I feel like it could lead to something as we’ve both agreed to go on a date, although we can never seem to find a time that suits us both.

Recently, a rumor went around about us. My colleague made me aware of the rumor, and she said “it’s not the rumor that bothers me but who started it.” I’m really confused as to whether or not I actually have a shot with her. We’ve also been extremely close, telling each other everything for nearly three years. Please help.

—Maybe

Dear Maybe,

I’m sorry to say this but I don’t think your colleague wants this to lead to something as much as you do. I’m not saying she doesn’t like you and like talking to you. She clearly does. But if she wanted to make time for a date with you, she would have done that. Enjoy the crush and how it makes work more fun. But stop pushing and look elsewhere for romance.

Classic Prudie

I’ve always been interested in doing some form of sex work. I think I’d be good at it and would enjoy it. I’ve thought about doing some sugar babying in the past but never gone through with it. Recently, I’ve been wanting to start an OnlyFans account. The only issue is I teach college.